Iodine-mediated ring-closing iodoamination with concomitant N-debenzylation for the asymmetric synthesis of polyhydroxylated pyrrolidines

Stephen G. Davies; Rebecca L. Nicholson; Paul D. Price; Paul M. Roberts; Angela J. Russell; Edward D. Savory; Andrew D. Smith; James E. Thomson

doi:10.1016/j.tetasy.2009.02.014

Iodine-mediated ring-closing iodoamination with concomitant N-debenzylation for the asymmetric synthesis of polyhydroxylated pyrrolidines

Stephen G. Davies, Rebecca L. Nicholson, Paul D. Price, Paul M. Roberts, Angela J. Russell, Edward D. Savory, Andrew D. Smith, James E. Thomson

Research output: Contribution to journal › Article › peer-review

Abstract

Treatment of a range of homochiral unsaturated beta-amino esters (containing a cis-dioxolane unit) with iodine promotes a novel ring-closing alkene iodoamination reaction which proceeds with concomitant N-debenzylation, providing a simple and stereoselective route to iodomethyl pyrrolidines. Functional group interconversion of the resulting iodomethyl pyrrolidines upon treatment with AgOAc proceeds via the corresponding aziridinium ion, with Subsequent deprotection giving access to polyhydroxylated pyrrolidines. (C) 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	758-772
Number of pages	15
Journal	Tetrahedron: Asymmetry
Volume	20
Issue number	6-8
DOIs	https://doi.org/10.1016/j.tetasy.2009.02.014
Publication status	Published - 7 May 2009

Keywords

JASPINE-B PACHASTRISSAMINE
HOMOCHIRAL LITHIUM AMIDES
D-LYXO-PHYTOSPHINGOSINE
CONJUGATE ADDITION
(2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID
STEREOSELECTIVE-SYNTHESIS
GLYCOSIDASE INHIBITORS
ORGANIC-SYNTHESIS
AMINO-ACIDS
ROUTE

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10.1016/j.tetasy.2009.02.014

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@article{235c57c3081e49e7bebfae0841e84507,

title = "Iodine-mediated ring-closing iodoamination with concomitant N-debenzylation for the asymmetric synthesis of polyhydroxylated pyrrolidines",

abstract = "Treatment of a range of homochiral unsaturated beta-amino esters (containing a cis-dioxolane unit) with iodine promotes a novel ring-closing alkene iodoamination reaction which proceeds with concomitant N-debenzylation, providing a simple and stereoselective route to iodomethyl pyrrolidines. Functional group interconversion of the resulting iodomethyl pyrrolidines upon treatment with AgOAc proceeds via the corresponding aziridinium ion, with Subsequent deprotection giving access to polyhydroxylated pyrrolidines. (C) 2009 Elsevier Ltd. All rights reserved.",

keywords = "JASPINE-B PACHASTRISSAMINE, HOMOCHIRAL LITHIUM AMIDES, D-LYXO-PHYTOSPHINGOSINE, CONJUGATE ADDITION, (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID, STEREOSELECTIVE-SYNTHESIS, GLYCOSIDASE INHIBITORS, ORGANIC-SYNTHESIS, AMINO-ACIDS, ROUTE",

author = "Davies, {Stephen G.} and Nicholson, {Rebecca L.} and Price, {Paul D.} and Roberts, {Paul M.} and Russell, {Angela J.} and Savory, {Edward D.} and Smith, {Andrew D.} and Thomson, {James E.}",

year = "2009",

month = may,

day = "7",

doi = "10.1016/j.tetasy.2009.02.014",

language = "English",

volume = "20",

pages = "758--772",

journal = "Tetrahedron: Asymmetry",

issn = "0957-4166",

publisher = "Elsevier",

number = "6-8",

}

TY - JOUR

T1 - Iodine-mediated ring-closing iodoamination with concomitant N-debenzylation for the asymmetric synthesis of polyhydroxylated pyrrolidines

AU - Davies, Stephen G.

AU - Nicholson, Rebecca L.

AU - Price, Paul D.

AU - Roberts, Paul M.

AU - Russell, Angela J.

AU - Savory, Edward D.

AU - Smith, Andrew D.

AU - Thomson, James E.

PY - 2009/5/7

Y1 - 2009/5/7

N2 - Treatment of a range of homochiral unsaturated beta-amino esters (containing a cis-dioxolane unit) with iodine promotes a novel ring-closing alkene iodoamination reaction which proceeds with concomitant N-debenzylation, providing a simple and stereoselective route to iodomethyl pyrrolidines. Functional group interconversion of the resulting iodomethyl pyrrolidines upon treatment with AgOAc proceeds via the corresponding aziridinium ion, with Subsequent deprotection giving access to polyhydroxylated pyrrolidines. (C) 2009 Elsevier Ltd. All rights reserved.

AB - Treatment of a range of homochiral unsaturated beta-amino esters (containing a cis-dioxolane unit) with iodine promotes a novel ring-closing alkene iodoamination reaction which proceeds with concomitant N-debenzylation, providing a simple and stereoselective route to iodomethyl pyrrolidines. Functional group interconversion of the resulting iodomethyl pyrrolidines upon treatment with AgOAc proceeds via the corresponding aziridinium ion, with Subsequent deprotection giving access to polyhydroxylated pyrrolidines. (C) 2009 Elsevier Ltd. All rights reserved.

KW - JASPINE-B PACHASTRISSAMINE

KW - HOMOCHIRAL LITHIUM AMIDES

KW - D-LYXO-PHYTOSPHINGOSINE

KW - CONJUGATE ADDITION

KW - (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID

KW - STEREOSELECTIVE-SYNTHESIS

KW - GLYCOSIDASE INHIBITORS

KW - ORGANIC-SYNTHESIS

KW - AMINO-ACIDS

KW - ROUTE

U2 - 10.1016/j.tetasy.2009.02.014

DO - 10.1016/j.tetasy.2009.02.014

M3 - Article

SN - 0957-4166

VL - 20

SP - 758

EP - 772

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 6-8

ER -

Iodine-mediated ring-closing iodoamination with concomitant N-debenzylation for the asymmetric synthesis of polyhydroxylated pyrrolidines

Abstract

Keywords

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